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Cesium carbonate → 6-(benzyloxy)-N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamide

HRID 1961477
ノート
印刷プレビュー

反応式

HRID 1961477 の反応式
[C:1]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:14]([CH3:24])=[N:15][C:16]3[C:21]([CH:22]=2)=[CH:20][C:19](I)=[CH:18][N:17]=3)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:27]([O-:30])([O-])=O.[Cs+].[Cs+].CC1C=N[C:37]2[C:46](C=1C)=[CH:45][CH:44]=[C:43]1[C:38]=2N=CC(C)=C1C>C(O)C1C=CC=CC=1.[Cu]I>[CH2:27]([O:30][C:19]1[CH:20]=[C:21]2[C:16](=[N:17][CH:18]=1)[N:15]=[C:14]([CH3:24])[C:13]([C:11]([NH:10][CH2:9][C:8]1[CH:25]=[CH:26][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=1)=[O:12])=[CH:22]2)[C:37]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:38]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 66746137N-(4-tert-butylbenzyl)-6-iodo-2-methyl-1,8-naphthyridine-3-carboxamide

生成物 1

HCID 667454906-(benzyloxy)-N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamide収率 235.1%

試薬・触媒・溶媒 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 244Benzyl Alcohol溶媒

反応条件

温度
120 °C

実験手順

In a screw cap pressure tube were N-(4-tert-butylbenzyl)-6-iodo-2-methyl-1,8-naphthyridine-3-carboxamide (135 mg, 0.30 mmol), Cs2CO3 (191.5 mg, 0.6 mmol), CuI (5.6 mg, 0.03 mmol) and 3,4,7,8-tetramethyl-1,10-phenantroline (14.0 mg, 0.06 mmol)) suspended in benzyl alcohol (4.5 ml). N2 was bubbled through the suspension for 5 min. The tube was sealed and the mixture heated to 120° C. overnight. The mixture was allowed to cool. CH2Cl2 was added and the mixture washed with H2O, dried (MgSO4), filtered and concentrated. The crude mixture was purified by flash chromatography (CH2Cl2/MeOH 98:2→97:3) yielding 62 mg of the title compound (47%).

後処理

  1. customIn a screw cap pressure tube
  2. customN2 was bubbled through the suspension for 5 min
  3. customThe tube was sealed
  4. temperatureto cool
  5. additionCH2Cl2 was added
  6. washthe mixture washed with H2O
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude mixture was purified by flash chromatography (CH2Cl2/MeOH 98:2→97:3)

出典と根拠

ORDレコード
ord-6d277d7471d1496ab58ea35c98806e13
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08415333B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート